NP-MRD: Showing NP-Card for 12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate (NP0167812)

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Record Information

Version

2.0

Created at

2022-09-03 03:28:52 UTC

Updated at

2022-09-03 03:28:52 UTC

NP-MRD ID

NP0167812

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate

Description

12,14-Bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]Pentadec-6-en-10-yl butanoate belongs to the class of organic compounds known as briarane diterpenoids. These are marine diterpenoids with a structure based on the briarane (3,8-cyclocembrane) skeleton. 12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate is found in Briareum asbestinum. Based on a literature review very few articles have been published on 12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]Pentadec-6-en-10-yl butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205282D          

 39 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032205282D          

 39 41  0  0  0  0            999 V2000
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    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3941   -1.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
  7 38  1  0  0  0  0
 24 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167812

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OC1CCC(C)=CC2OC2(C(C)C(=O)OC)C(=O)C2C(C)C(CC(OC(C)=O)C12C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O10/c1-9-10-24(32)38-21-12-11-15(2)13-23-29(39-23,17(4)27(34)35-8)26(33)25-16(3)20(36-18(5)30)14-22(28(21,25)7)37-19(6)31/h13,16-17,20-23,25H,9-12,14H2,1-8H3

> <INCHI_KEY>
NGLUOUFRVZNZPM-UHFFFAOYSA-N

> <FORMULA>
C29H42O10

> <MOLECULAR_WEIGHT>
550.645

> <EXACT_MASS>
550.277797552

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.31684436546929

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0^{3,5}]pentadec-6-en-10-yl butanoate

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
3.4671671789999996

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.7962746544348

> <JCHEM_PKA_STRONGEST_BASIC>
-4.315128411260801

> <JCHEM_POLAR_SURFACE_AREA>
134.8

> <JCHEM_REFRACTIVITY>
138.1408

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0^{3,5}]pentadec-6-en-10-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.338   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.774  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.935  -2.865   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.314  -1.334   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      19.084  -0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      19.084  -2.667   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.624  -2.667   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.139  -0.931   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.536  -3.241   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   38                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13   16   22                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   15   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   38                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33    7   24   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
12,14-Bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0,]pentadec-6-en-10-yl butanoic acid	Generator

Chemical Formula

C₂₉H₄₂O₁₀

Average Mass

550.6450 Da

Monoisotopic Mass

550.27780 Da

IUPAC Name

12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0^{3,5}]pentadec-6-en-10-yl butanoate

Traditional Name

12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0^{3,5}]pentadec-6-en-10-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OC1CCC(C)=CC2OC2(C(C)C(=O)OC)C(=O)C2C(C)C(CC(OC(C)=O)C12C)OC(C)=O

InChI Identifier

InChI=1S/C29H42O10/c1-9-10-24(32)38-21-12-11-15(2)13-23-29(39-23,17(4)27(34)35-8)26(33)25-16(3)20(36-18(5)30)14-22(28(21,25)7)37-19(6)31/h13,16-17,20-23,25H,9-12,14H2,1-8H3

InChI Key

NGLUOUFRVZNZPM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Briareum asbestinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as briarane diterpenoids. These are marine diterpenoids with a structure based on the briarane (3,8-cyclocembrane) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Briarane diterpenoids

Alternative Parents

Substituents

Briarane diterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Methyl ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.39	ALOGPS
logP	3.47	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.8	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	134.8 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.14 m³·mol⁻¹	ChemAxon
Polarizability	57.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73818027

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate (NP0167812)

MOL for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

3D MOL for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

3D SDF for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

3D-SDF for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

PDB for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

3D PDB for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

SMILES for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

INCHI for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

Structure for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)

3D Structure for NP0167812 (12,14-bis(acetyloxy)-3-(1-methoxy-1-oxopropan-2-yl)-7,11,15-trimethyl-2-oxo-4-oxatricyclo[9.4.0.0³,⁵]pentadec-6-en-10-yl butanoate)